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My Blueberry workhorse needs a new HD and OS X - it can't get on the Internet with OS 9 anymore, at least not wirelessly. Any suggestions on a version of OS X to try to run on it? Does anyone have any experience taking this (or a Strawberry iMac, for that matter) to OS X. I know about the first 6 GB limitation for the early versions of the OS, but anything else I should consider?

The last version of OS X you can install is Tiger. In my own experience, performance was about the same between Panther and Tiger, and the addition of Spotlight makes Tiger worth the upgrade.

That being said...any version of OS X on a 300MHz clamshell is going to run like total shit. It's painfully slow. Painful. It's mostly because the CPU has only 512k L2 cache, and the GPU is given only 4MB VRAM. Even with a 512MB stick of RAM installed, it's just going to run really, really, really slowly.

In my own experiences with G3 Macs, OS 9 runs like butter compared to OS X. I would seriously recommend looking at either adding a cheap 802.11b router to your network (segregated from everything else if you're really worried) with WEP set up, or see if your wireless router supports DD-WRT - if it does, flash that baby and get a second, WEP network going for your old Macs! It's totally worth it.

Aside from no Flash support, Classilla in OS 9 is fantastic. It supports most modern browser technologies (although I don't know for sure if it supports fancy HTML5 stuff yet) and renders pages pretty damn well for running on an ancient OS.

If you're dead-set on running OS X, stick with Tiger and you should be okay. There are no hard drive partition limitations that I can recall, although my own clamshell has a 466MHz board in it, which is different enough that I'd Google to make sure if I were you.

Let's see.....

Are you willing to invest a little money in a few upgrades to make it as powerful as you can?

ETA: Join Maclassic while you're at it, if you haven't. This is the kind of stuff I created the site for.

ETA2: Also, have you considered Linux? I am not one to use Linux as a primary OS on any machine, but I had Debian Wheezy (I think? Whatever the latest release was a few months ago) running on an old PowerBook G4, and it was much more useable than OS X, because of how obsolete Tiger has become.

My experience with OS X on older Macs - a 400 MHz iMac DV, in my case - was that the deciding factor is RAM. 512 MB or don't bother, and Tiger was probably the best of them. Consider disabling the Dashboard. It is worth noting that the GPU in an iBook is even slower than the Rage 128 in my old iMac, but that's mostly about how the effects run. Tone them down as best you can (disable the genie effect for the Dock, for instance). Video RAM is irrelevant, however - compositing isn't on the GPU anyway, you need at least the first Radeon for that.

The new Mac Pro has up to 30 MB of cache inside the processor itself. That's more than the HD in my first Mac. Somehow I'm still running out of space.

You're going to have a pretty awful Internet experience no matter what OS you put on that machine -- too much of the web has moved on, unless you're a major fan of IRC, Usenet and e-mail.

If I had an iBook of that vintage in the house I'd give it the last version of OS 9, Classzilla as someone suggested and load it up with OS 9 software and keep it just for that. I don't see much point in trying to run OS X on those machines. They can still be useful -- a writer friend of mine still uses my old charcoal iBook for writing and emailing -- but only in very limited ways or with contemporaneous software for the era in which it was released.